Reaktion #8714

Reaktionsgleichung

NaH

2-(4-bromo-phenoxy)-ethanol

2-phenyl-ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide

→

2-phenyl-ethanesulfonic acid {6-[2-(4-bromo-phenoxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

Ausbeute 86.7%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued at 70° C. for 12 h and at rt for 72 h
4. 4
   SonstigeThe solvent was evaporated
5. 5
   workup.ADDITIONThe residue was treated with water (40 ml)
6. 6
   Extraktionextracted twice with EA (50 ml)
7. 7
   WaschenThe organic phase was washed with water
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe crude product was crystallised from 2-propanol

Vorschrift

To a suspension of NaH (17 mg, 60% in mineral oil) in DME (5 ml) was added 2-(4-bromo-phenoxy)-ethanol (111 mg). The mixture was stirred at 50° C. for 1 h before 2-phenyl-ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (100 mg, Referential Example 1f) and K-tert.-butylate (25 mg) was added. The mixture was stirred at 70° C. for 16 h. A further portion of K-tert.-butylate (50 mg) was added and stirring was continued at 70° C. for 12 h and at rt for 72 h. The solvent was evaporated. The residue was treated with water (40 ml), acidified with 10% aq. citric acid and extracted twice with EA (50 ml). The organic phase was washed with water and evaporated. The crude product was crystallised from 2-propanol to give 2-phenyl-ethanesulfonic acid {6-[2-(4-bromo-phenoxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (127 mg) as a beige powder. LC-MS: tR=6.14 min, [M+1]+=568.38, [M−1]−=570.15.

Quelle